Lavendustin A | RG 14355 | CAS#125697-92-9 | EGFR inhibitor

Lavendustin A
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 407367

CAS#: 125697-92-9

Description: Lavendustin A, also known as RG 14355, is a potent, cell-permeable inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase (IC50 = 11 nM). Lavendustin A shows cytotoxic effects on tumor cell lines. Lavendustin A enhances axon elongation in VHL gene-transfected neural stem cells.

Chemical Structure

Lavendustin A

CAS# 125697-92-9

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 407367
Name: Lavendustin A
CAS#: 125697-92-9
Chemical Formula: C21H19NO6
Exact Mass: 381.12
Molecular Weight: 381.384
Elemental Analysis: C, 66.14; H, 5.02; N, 3.67; O, 25.17

Price and Availability

Size	Price	Availability
5mg	USD 385	2 Weeks
10mg	USD 710	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: Lavendustin A; RG 14355; RG-14355; RG14355.

IUPAC/Chemical Name: 5-[[(2,5-Dihydroxyphenyl)methyl][(2-hydroxyphenyl)methyl]amino]-2-hydroxybenzoic acid

InChi Key: ULTTYPMRMMDONC-UHFFFAOYSA-N

InChi Code: InChI=1S/C21H19NO6/c23-16-6-8-19(25)14(9-16)12-22(11-13-3-1-2-4-18(13)24)15-5-7-20(26)17(10-15)21(27)28/h1-10,23-26H,11-12H2,(H,27,28)

SMILES Code: O=C(O)C1=CC(N(CC2=CC(O)=CC=C2O)CC3=CC=CC=C3O)=CC=C1O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

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Product Data:

Product Data

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Biological target:	Lavendustin A (RG-14355) is a potent, selective and ATP-competitive inhibitor of epidermal growth factor receptor (EGFR) tyrosine kinase, with an IC50 of 11 nM.
In vitro activity:	Lavendustin A and genistein selectively blocked the induction of LTP when applied in the bath or injected into the postsynaptic cell. Reference: Nature. 1991 Oct 10;353(6344):558-60. https://pubmed.ncbi.nlm.nih.gov/1656271/
In vivo activity:	Lavendustin A, a potent inhibitor of protein tyrosine kinases, at the concentrations of 0.5 and 1.3 microM decreased atrial wall stretch-induced ANP secretion (53% and 68%, respectively, P < 0.001) in the perfused rat heart preparation, whereas no difference in the hemodynamic variables (heart rate, contractile force and perfusion pressure) were noted between groups. Lavendustin A also completely abolished the wall stretch-induced secretion of BNP. Reference: Endocrinology. 1999 Sep;140(9):4198-207. https://pubmed.ncbi.nlm.nih.gov/10465292/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	20.0	52.44
	DMF:PBS (pH 7.2) (1:1)	0.5	1.31
	DMSO	20.0	52.44
	Ethanol	10.0	26.22

Preparing Stock Solutions

The following data is based on the product molecular weight 381.38 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:	1. O'Dell TJ, Kandel ER, Grant SG. Long-term potentiation in the hippocampus is blocked by tyrosine kinase inhibitors. Nature. 1991 Oct 10;353(6344):558-60. doi: 10.1038/353558a0. PMID: 1656271. 2. Onoda T, Iinuma H, Sasaki Y, Hamada M, Isshiki K, Naganawa H, Takeuchi T, Tatsuta K, Umezawa K. Isolation of a novel tyrosine kinase inhibitor, lavendustin A, from Streptomyces griseolavendus. J Nat Prod. 1989 Nov-Dec;52(6):1252-7. doi: 10.1021/np50066a009. PMID: 2614420. 3. Whitehead SA, Lacey M. Protein tyrosine kinase activity of lavendustin A and the phytoestrogen genistein on progesterone synthesis in cultured rat ovarian cells. Fertil Steril. 2000 Mar;73(3):613-9. doi: 10.1016/s0015-0282(99)00580-4. PMID: 10689022. 4. Taskinen P, Toth M, Vuolteenaho O, Magga J, Ruskoaho H. Inhibition of atrial wall stretch-induced cardiac hormone secretion by lavendustin A, a potent tyrosine kinase inhibitor. Endocrinology. 1999 Sep;140(9):4198-207. doi: 10.1210/endo.140.9.6967. PMID: 10465292.
In vitro protocol:	1. O'Dell TJ, Kandel ER, Grant SG. Long-term potentiation in the hippocampus is blocked by tyrosine kinase inhibitors. Nature. 1991 Oct 10;353(6344):558-60. doi: 10.1038/353558a0. PMID: 1656271. 2. Onoda T, Iinuma H, Sasaki Y, Hamada M, Isshiki K, Naganawa H, Takeuchi T, Tatsuta K, Umezawa K. Isolation of a novel tyrosine kinase inhibitor, lavendustin A, from Streptomyces griseolavendus. J Nat Prod. 1989 Nov-Dec;52(6):1252-7. doi: 10.1021/np50066a009. PMID: 2614420.
In vivo protocol:	1. Whitehead SA, Lacey M. Protein tyrosine kinase activity of lavendustin A and the phytoestrogen genistein on progesterone synthesis in cultured rat ovarian cells. Fertil Steril. 2000 Mar;73(3):613-9. doi: 10.1016/s0015-0282(99)00580-4. PMID: 10689022. 2. Taskinen P, Toth M, Vuolteenaho O, Magga J, Ruskoaho H. Inhibition of atrial wall stretch-induced cardiac hormone secretion by lavendustin A, a potent tyrosine kinase inhibitor. Endocrinology. 1999 Sep;140(9):4198-207. doi: 10.1210/endo.140.9.6967. PMID: 10465292.

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1: Nam DH, Lee KY, Moon CS, Lee YS. Synthesis and anticancer activity of chromone-based analogs of lavendustin A. Eur J Med Chem. 2010 Sep;45(9):4288-92. doi: 10.1016/j.ejmech.2010.06.030. PubMed PMID: 20630626.

2: Löber K, Alfonso A, Escribano L, Botana LM. Influence of the tyrosine kinase inhibitors STI571 (Glivec), lavendustin A and genistein on human mast cell line (HMC-1(560)) activation. J Cell Biochem. 2008 Mar 1;103(4):1076-88. PubMed PMID: 17661356.

3: Lee KY, Nam DH, Moon CS, Seo SH, Lee JY, Lee YS. Synthesis and anticancer activity of lavendustin A derivatives containing arylethenylchromone substituents. Eur J Med Chem. 2006 Aug;41(8):991-6. PubMed PMID: 16762460.

4: Mu F, Hamel E, Lee DJ, Pryor DE, Cushman M. Synthesis, anticancer activity, and inhibition of tubulin polymerization by conformationally restricted analogues of lavendustin A. J Med Chem. 2003 Apr 24;46(9):1670-82. PubMed PMID: 12699385.

5: Nussbaumer P, Winiski AP. Structure-activity relationship studies on a novel class of antiproliferative agents derived from Lavendustin A. Part I: Ring A modifications. Bioorg Med Chem. 2008 Aug 15;16(16):7552-60. doi: 10.1016/j.bmc.2008.07.039. PubMed PMID: 18678497.

6: Albuschat R, Löwe W, Weber M, Luger P, Jendrossek V. 4-Anilinoquinazolines with Lavendustin A subunit as inhibitors of epidermal growth factor receptor tyrosine kinase: syntheses, chemical and pharmacological properties. Eur J Med Chem. 2004 Dec;39(12):1001-11. PubMed PMID: 15571862.

7: Mu F, Lee DJ, Pryor DE, Hamel E, Cushman M. Synthesis and investigation of conformationally restricted analogues of lavendustin A as cytotoxic inhibitors of tubulin polymerization. J Med Chem. 2002 Oct 10;45(21):4774-85. PubMed PMID: 12361405.

8: Murakami K, Kanno H, Yamamoto I, Saito T. Lavendustin A enhances axon elongation in VHL gene-transfected neural stem cells. Neuroreport. 2004 Mar 22;15(4):611-4. PubMed PMID: 15094462.

9: Mu F, Coffing SL, Riese DJ 2nd, Geahlen RL, Verdier-Pinard P, Hamel TE, Johnson J, Cushman M. Design, synthesis, and biological evaluation of a series of lavendustin A analogues that inhibit EGFR and Syk tyrosine kinases, as well as tubulin polymerization. J Med Chem. 2001 Feb 1;44(3):441-52. PubMed PMID: 11462983.

10: Seki T, Yokoshiki H, Sunagawa M, Nakamura M, Sperelakis N. Angiotensin II stimulation of Ca2+-channel current in vascular smooth muscle cells is inhibited by lavendustin-A and LY-294002. Pflugers Arch. 1999 Feb;437(3):317-23. PubMed PMID: 9914387.

11: Taskinen P, Toth M, Vuolteenaho O, Magga J, Ruskoaho H. Inhibition of atrial wall stretch-induced cardiac hormone secretion by lavendustin A, a potent tyrosine kinase inhibitor. Endocrinology. 1999 Sep;140(9):4198-207. PubMed PMID: 10465292.

12: Hisatomi M, Hayakawa T, Hidaka H, Niki I. Modulation of tyrosine kinase activity has multiple actions on insulin release from the pancreatic beta-cell: studies with lavendustin A. Jpn J Pharmacol. 1997 Jun;74(2):203-8. PubMed PMID: 9243329.

13: Whitehead SA, Lacey M. Protein tyrosine kinase activity of lavendustin A and the phytoestrogen genistein on progesterone synthesis in cultured rat ovarian cells. Fertil Steril. 2000 Mar;73(3):613-9. PubMed PMID: 10689022.

14: Whitehead SA, Cross JE, Burden C, Lacey M. Acute and chronic effects of genistein, tyrphostin and lavendustin A on steroid synthesis in luteinized human granulosa cells. Hum Reprod. 2002 Mar;17(3):589-94. PubMed PMID: 11870108.

15: Cammisuli S, Winiski A, Nussbaumer P, Hiestand P, Stütz A, Weckbecker G. SDZ 281-977: a modified partial structure of lavendustin A that exerts potent and selective antiproliferative activities in vitro and in vivo. Int J Cancer. 1996 Jan 26;65(3):351-9. PubMed PMID: 8575857.

16: Hu DE, Fan TP. Suppression of VEGF-induced angiogenesis by the protein tyrosine kinase inhibitor, lavendustin A. Br J Pharmacol. 1995 Jan;114(2):262-8. PubMed PMID: 7533611; PubMed Central PMCID: PMC1510224.

17: Meizel S, Turner KO. Chloride efflux during the progesterone-initiated human sperm acrosome reaction is inhibited by lavendustin A, a tyrosine kinase inhibitor. J Androl. 1996 Jul-Aug;17(4):327-30. PubMed PMID: 8889693.

18: Nussbaumer P, Winiski AP, Cammisuli S, Hiestand P, Weckbecker G, Stütz A. Novel antiproliferative agents derived from lavendustin A. J Med Chem. 1994 Nov 25;37(24):4079-84. PubMed PMID: 7990108.

19: Hsu CY, Persons PE, Spada AP, Bednar RA, Levitzki A, Zilberstein A. Kinetic analysis of the inhibition of the epidermal growth factor receptor tyrosine kinase by Lavendustin-A and its analogue. J Biol Chem. 1991 Nov 5;266(31):21105-12. PubMed PMID: 1939153.

20: Ebel D, Müllenheim J, Südkamp H, Bohlen T, Ferrari J, Huhn R, Preckel B, Schlack W. Role of tyrosine kinase in desflurane-induced preconditioning. Anesthesiology. 2004 Mar;100(3):555-61. PubMed PMID: 15108968.

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Lavendustin A featured